{"corpus_id":105096151,"paper_sha":"14579a901844a2af56086b1e88bfa9bbb8068392","doi":"10.1080/10426507.2018.1487432","arxiv_id":null,"pmid":null,"pmcid":null,"mag_id":2883324693,"dblp_id":null,"acl_id":null,"title":"Bifunctionalized allenes. Part XXI. Electrophilic cyclization and addition reactions of 3-(α- or β-hydroxyalkyl)-allenylphosphonates and allenyl phosphine oxides","year":2018,"publication_date":"2018-10-03","venue":"Phosphorus Sulfur and Silicon and the Related Elements","journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","pages":"611 - 619","volume":"193"},"journal_issn":null,"journal_title":null,"publication_types":[],"pubmed_pub_types":null,"s2_fields_of_study":["Chemistry"],"reference_count":37,"citation_count":3,"influential_citation_count":0,"is_open_access":false,"arxiv_categories":null,"arxiv_license":null,"arxiv_journal_ref":null,"mesh_headings":null,"chemicals":null,"comments_corrections":null,"source_flags":1,"s2_open_access_pdf_url":null,"s2_open_access_landing_url":null,"s2_open_access_license":null,"s2_open_access_status":null,"pmc_open_access_pdf_url":null,"pmc_open_access_landing_url":null,"pmc_open_access_license":null,"pmc_open_access_status":null,"unpaywall_open_access_pdf_url":null,"unpaywall_open_access_landing_url":null,"unpaywall_open_access_license":null,"unpaywall_open_access_status":null,"abstract":"Abstract The present paper discusses the electrophilic cyclization and addition reactions of 3-(α- or β-hydroxyalkyl)-allenylphosphonates and phosphine oxides. Treatment of 3-(α- or β-hydroxy-alkyl)-allenylphosphonates with electrophiles takes place with 5-endo-trig cyclization and gives 2-methoxy-2,5-dihydro-1,2-oxaphosphole 2-oxides as a result of the neighboring phosphonate group participation in the electrophilic cyclization. On the other hand, 3-(α- or β-hydroxyalkyl)-alk-(1E)-en-1-yl phosphine oxides were prepared by chemo-, regio-, and stereoselective electrophilic addition to the C2-C3-double bond in the 3-(α- or β-hydroxyalkyl)-alka-1,2-dienyl phosphine oxides and subsequent attack of the external nucleophile (halide anion). The paper proposes a possible mechanism that involves electrophilic cyclization and addition reactions of the phosphorylated (α- or β-hydroxyalkyl)allenes. Graphical Abstract","claims":[{"public_id":"cl_00ebde773449352f6817eb8f8e55ddd3","status":"active","text":"3-(α- or β-hydroxyalkyl)-alk-(1E)-en-1-yl phosphine oxides are formed by chemo-, regio-, and stereoselective electrophilic addition to the C2-C3 double bond of 3-(α- or β-hydroxyalkyl)-alka-1,2-dienyl phosphine oxides followed by attack of an external halide anion.","confidence":0.97,"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/claims/cl_00ebde773449352f6817eb8f8e55ddd3"},{"public_id":"cl_383967c93a9a6c67199a7a0f6e015ca9","status":"active","text":"A possible mechanism involving electrophilic cyclization and addition reactions of phosphorylated (α- or β-hydroxyalkyl)allenes is proposed.","confidence":0.9,"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/claims/cl_383967c93a9a6c67199a7a0f6e015ca9"},{"public_id":"cl_44e8f0d707a4ced650139b4af37e1f52","status":"active","text":"Neighboring phosphonate group participation drives the electrophilic cyclization of 3-(α- or β-hydroxyalkyl)-allenylphosphonates.","confidence":0.93,"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/claims/cl_44e8f0d707a4ced650139b4af37e1f52"},{"public_id":"cl_c9937dd0653a5271aeea7b3d97ce3dd1","status":"active","text":"Treatment of 3-(α- or β-hydroxyalkyl)-allenylphosphonates with electrophiles proceeds by 5-endo-trig cyclization to give 2-methoxy-2,5-dihydro-1,2-oxaphosphole 2-oxides.","confidence":0.98,"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous 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